Triethylamine → Imidazo[1,2-a]pyridine,5-[(4-chlorobutyl)thio]-

HRID 357000

Reaction equation

HRID 357000 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][Cl:6].[SH:7][C:8]1[N:13]2[CH:14]=[CH:15][N:16]=[C:12]2[CH:11]=[CH:10][CH:9]=1.C(N(CC)CC)C>C(O)C>[Cl:6][CH2:5][CH2:4][CH2:3][CH2:2][S:7][C:8]1[N:13]2[CH:14]=[CH:15][N:16]=[C:12]2[CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 813641-Bromo-4-chlorobutaneHCID 178418687HCID 178418687, compound

Product 1

HCID 18936641Imidazo[1,2-a]pyridine,5-[(4-chlorobutyl)thio]-

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a nitrogen atmosphere, 8.87 ml (77 mmol) of 1-bromo-4-chlorobutane was added to a solution of 10.51 g (70 mmol) of 5-mercaptoimidazo[1,2-a]pyridine and 10.73 ml (77 mmol) of triethylamine in 150 ml of ethanol was added, followed by stirring at room temperature for 16 hours. After the solvent was distilled off, the residue was dissolved in dichloromethane. This solution was washed with saturated aqueous sodium hydrogen carbonate and dried, after which the solvent was distilled off. The residue was purified by column chromatography (eluent: ethyl acetate) to yield 12.93 g (76.7%, light brown oily substance) of the desired product.

Workup

  1. additionwas added
  2. distillationAfter the solvent was distilled off
  3. dissolutionthe residue was dissolved in dichloromethane
  4. washThis solution was washed with saturated aqueous sodium hydrogen carbonate
  5. customdried
  6. distillationafter which the solvent was distilled off
  7. customThe residue was purified by column chromatography (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-afc7370ad75e49a9ac250316b96f5076
Source dataset
uspto-grants-1998_11
Patent number
US05840732

Linked notes

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